EP3969516B1 - Composition de silicone pouvant être réticulée pour former une matière composite de résine de silicone - Google Patents
Composition de silicone pouvant être réticulée pour former une matière composite de résine de silicone Download PDFInfo
- Publication number
- EP3969516B1 EP3969516B1 EP19725152.3A EP19725152A EP3969516B1 EP 3969516 B1 EP3969516 B1 EP 3969516B1 EP 19725152 A EP19725152 A EP 19725152A EP 3969516 B1 EP3969516 B1 EP 3969516B1
- Authority
- EP
- European Patent Office
- Prior art keywords
- radical
- units
- mol
- fillers
- silicone resin
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 239000000203 mixture Substances 0.000 title claims description 23
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- 239000011342 resin composition Substances 0.000 claims description 17
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- 239000012765 fibrous filler Substances 0.000 claims description 11
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 10
- 229910052710 silicon Inorganic materials 0.000 claims description 10
- 229930195735 unsaturated hydrocarbon Natural products 0.000 claims description 10
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- IQYMRQZTDOLQHC-ZQTLJVIJSA-N [(1R,4S)-2-bicyclo[2.2.1]heptanyl] prop-2-enoate Chemical compound C1C[C@H]2C(OC(=O)C=C)C[C@@H]1C2 IQYMRQZTDOLQHC-ZQTLJVIJSA-N 0.000 description 2
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- MJSNUBOCVAKFIJ-LNTINUHCSA-N chromium;(z)-4-oxoniumylidenepent-2-en-2-olate Chemical compound [Cr].C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O MJSNUBOCVAKFIJ-LNTINUHCSA-N 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 229910052906 cristobalite Inorganic materials 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- 150000001925 cycloalkenes Chemical class 0.000 description 1
- ZXIJMRYMVAMXQP-UHFFFAOYSA-N cycloheptene Chemical compound C1CCC=CCC1 ZXIJMRYMVAMXQP-UHFFFAOYSA-N 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- CJBOPISUMAZJPD-UHFFFAOYSA-N cyclopropane;platinum Chemical compound [Pt].C1CC1 CJBOPISUMAZJPD-UHFFFAOYSA-N 0.000 description 1
- PPSZHCXTGRHULJ-UHFFFAOYSA-N dioxazine Chemical compound O1ON=CC=C1 PPSZHCXTGRHULJ-UHFFFAOYSA-N 0.000 description 1
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- 238000009826 distribution Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000010292 electrical insulation Methods 0.000 description 1
- 229910052675 erionite Inorganic materials 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000006266 etherification reaction Methods 0.000 description 1
- SUPCQIBBMFXVTL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=C SUPCQIBBMFXVTL-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 239000007850 fluorescent dye Substances 0.000 description 1
- 239000012634 fragment Substances 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 229910021485 fumed silica Inorganic materials 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 239000006232 furnace black Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 239000010440 gypsum Substances 0.000 description 1
- 229910052602 gypsum Inorganic materials 0.000 description 1
- 210000004209 hair Anatomy 0.000 description 1
- 239000012760 heat stabilizer Substances 0.000 description 1
- 230000008642 heat stress Effects 0.000 description 1
- 239000011487 hemp Substances 0.000 description 1
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000012761 high-performance material Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 229940097275 indigo Drugs 0.000 description 1
- COHYTHOBJLSHDF-UHFFFAOYSA-N indigo powder Natural products N1C2=CC=CC=C2C(=O)C1=C1C(=O)C2=CC=CC=C2N1 COHYTHOBJLSHDF-UHFFFAOYSA-N 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 235000013980 iron oxide Nutrition 0.000 description 1
- YOBAEOGBNPPUQV-UHFFFAOYSA-N iron;trihydrate Chemical compound O.O.O.[Fe].[Fe] YOBAEOGBNPPUQV-UHFFFAOYSA-N 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- PXZQEOJJUGGUIB-UHFFFAOYSA-N isoindolin-1-one Chemical compound C1=CC=C2C(=O)NCC2=C1 PXZQEOJJUGGUIB-UHFFFAOYSA-N 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000002372 labelling Methods 0.000 description 1
- MOUPNEIJQCETIW-UHFFFAOYSA-N lead chromate Chemical compound [Pb+2].[O-][Cr]([O-])(=O)=O MOUPNEIJQCETIW-UHFFFAOYSA-N 0.000 description 1
- 239000004611 light stabiliser Substances 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 125000005397 methacrylic acid ester group Chemical group 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000003094 microcapsule Substances 0.000 description 1
- 102000035118 modified proteins Human genes 0.000 description 1
- 108091005573 modified proteins Proteins 0.000 description 1
- 210000000050 mohair Anatomy 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 229920005615 natural polymer Polymers 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229920000620 organic polymer Polymers 0.000 description 1
- 150000001282 organosilanes Chemical class 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 229910052625 palygorskite Inorganic materials 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 150000003008 phosphonic acid esters Chemical group 0.000 description 1
- 150000003014 phosphoric acid esters Chemical group 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920000747 poly(lactic acid) Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920002312 polyamide-imide Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 1
- 239000004810 polytetrafluoroethylene Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- NHARPDSAXCBDDR-UHFFFAOYSA-N propyl 2-methylprop-2-enoate Chemical compound CCCOC(=O)C(C)=C NHARPDSAXCBDDR-UHFFFAOYSA-N 0.000 description 1
- PNXMTCDJUBJHQJ-UHFFFAOYSA-N propyl prop-2-enoate Chemical compound CCCOC(=O)C=C PNXMTCDJUBJHQJ-UHFFFAOYSA-N 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 239000004627 regenerated cellulose Substances 0.000 description 1
- 239000006254 rheological additive Substances 0.000 description 1
- 229910052895 riebeckite Inorganic materials 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 238000007142 ring opening reaction Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910052624 sepiolite Inorganic materials 0.000 description 1
- 235000019355 sepiolite Nutrition 0.000 description 1
- 125000005372 silanol group Chemical group 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- HBMJWWWQQXIZIP-UHFFFAOYSA-N silicon carbide Chemical compound [Si+]#[C-] HBMJWWWQQXIZIP-UHFFFAOYSA-N 0.000 description 1
- HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 235000019710 soybean protein Nutrition 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229920001059 synthetic polymer Polymers 0.000 description 1
- SJMYWORNLPSJQO-UHFFFAOYSA-N tert-butyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC(C)(C)C SJMYWORNLPSJQO-UHFFFAOYSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- ILJSQTXMGCGYMG-UHFFFAOYSA-N triacetic acid Chemical compound CC(=O)CC(=O)CC(O)=O ILJSQTXMGCGYMG-UHFFFAOYSA-N 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000010456 wollastonite Substances 0.000 description 1
- 229910052882 wollastonite Inorganic materials 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 125000005023 xylyl group Chemical group 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 235000014692 zinc oxide Nutrition 0.000 description 1
- NDKWCCLKSWNDBG-UHFFFAOYSA-N zinc;dioxido(dioxo)chromium Chemical compound [Zn+2].[O-][Cr]([O-])(=O)=O NDKWCCLKSWNDBG-UHFFFAOYSA-N 0.000 description 1
- RNWHGQJWIACOKP-UHFFFAOYSA-N zinc;oxygen(2-) Chemical class [O-2].[Zn+2] RNWHGQJWIACOKP-UHFFFAOYSA-N 0.000 description 1
- GFQYVLUOOAAOGM-UHFFFAOYSA-N zirconium(iv) silicate Chemical compound [Zr+4].[O-][Si]([O-])([O-])[O-] GFQYVLUOOAAOGM-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/14—Polysiloxanes containing silicon bound to oxygen-containing groups
- C08G77/16—Polysiloxanes containing silicon bound to oxygen-containing groups to hydroxyl groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/12—Polysiloxanes containing silicon bound to hydrogen
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/14—Peroxides
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/56—Organo-metallic compounds, i.e. organic compounds containing a metal-to-carbon bond
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K7/00—Use of ingredients characterised by shape
- C08K7/02—Fibres or whiskers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K7/00—Use of ingredients characterised by shape
- C08K7/02—Fibres or whiskers
- C08K7/04—Fibres or whiskers inorganic
- C08K7/14—Glass
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
- C08L83/04—Polysiloxanes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/20—Polysiloxanes containing silicon bound to unsaturated aliphatic groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/80—Siloxanes having aromatic substituents, e.g. phenyl side groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K2201/00—Specific properties of additives
- C08K2201/002—Physical properties
- C08K2201/005—Additives being defined by their particle size in general
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K2201/00—Specific properties of additives
- C08K2201/016—Additives defined by their aspect ratio
Definitions
- the invention relates to a silicone resin composition (S) which has silicone resin (i) with hydrogen radicals and olefinically unsaturated hydrocarbon radicals and contains both pulverulent fillers and fibrous fillers.
- Silicones are high-performance materials for many applications, especially for many electrical insulation tasks. They combine excellent UV resistance, resistance to heat stress, water repellency and resistance to hydrolysis. There is practically no organic polymer that can cover this combination of features. There are already a number of silicone resins in the form of a duromer, but their usability in the insulating parts industry is severely restricted due to the way they are administered (no finished products, not solvent-free).
- DE102015200704A1 describes the synthesis of pourable silicone resins with Si-H and Si-Vinyl units that can be cured by crosslinking with themselves.
- the object of the invention was to create filled silicone resin systems that can be processed with existing machines and technologies and have better mechanical properties after curing.
- the silicone resin composition (S) is particularly suitable for the production of moldings, since it can be ready-to-use, in particular 1-component, has a long pot life and low viscosity, can be used without solvents, can be processed with existing standard machines for resins and special labeling is not required .
- the silicone resin composition (S) is capable of self-crosslinking.
- the incorporation of the fibrous fillers is facilitated by the presence of the pulverulent fillers, and the processability of the silicone resin composition (S) is considerably improved compared with silicone resin compositions containing purely fibrous fillers.
- the latter have a felt-like consistency and cannot be processed into molded parts with reproducible properties.
- the silicone resin (i) can be prepared as described in DE102015200704A1 .
- the viscosity of the silicone resin (i) is preferably between 20 and 100,000 mPas, particularly preferably between 30 and 50,000 mPas, very particularly preferably between 50 and 10,000 mPas, in particular between 100 and 3,000 mPas. All information on viscosity is valid at 25°C and at normal pressure of 1013 mbar.
- the silicone resins (i) are preferably those which have a molecular weight Mw of at least 500, preferably at least 600, more preferably at least 700, in particular at least 800, the polydispersity being at most 20, preferably at most 18, more preferably at most 16, in particular at most 15 is.
- the silicone resin (i) preferably contains at least 10 mol%, particularly preferably at least 15 mol%, very particularly preferably at least 25 mol%, in particular at least 35 mol% and preferably at most 90 mol% of units of the general formula (Ic) .
- the silicone resin (i) preferably contains at least 25 mol %, particularly preferably at least 30 mol %, in particular at least 35 mol % and preferably at most 90 mol % of units of the general formula (Ia).
- the silicone resin (i) preferably contains not more than 15 mol %, particularly preferably not more than 10 mol %, in particular not more than 5 mol %, of units of the general formula (Ib).
- the silicone resin (i) preferably contains not more than 15 mol %, particularly preferably not more than 10 mol %, in particular not more than 5 mol %, of units of the general formula (Id).
- silicone resin (i) preferably at least 5 mol %, particularly preferably at least 10 mol %, in particular at least 15 mol %, of the units of the general formula (Ic) have an R 2 radical which is hydrogen.
- a radical R 2 which means olefinically unsaturated hydrocarbon radical.
- the ratio of radical R 2 which is an olefinically unsaturated hydrocarbon radical: radical R 2 , a hydrogen radical, is preferably 3:1 to 1:2, in particular 2:1 to 1: 1.1.
- organofunctional radicals R 2 are glycol radicals and functional organic groups from the group of phosphoric acid esters, phosphonic acid esters, epoxide functions, methacrylate functions, carboxyl functions, acrylate functions, olefinically or acetylenically unsaturated hydrocarbons or a hydridic silicon-bonded hydrogen.
- the respective functional groups can optionally be substituted.
- the radicals R 2 can optionally be hydroxy-, alkyloxy- or trimethylsilyl-terminated. In the main chain, non-adjacent carbon atoms can be replaced by oxygen atoms.
- the functional groups R 2 are generally not bonded directly to the silicon atom.
- An exception to this are the olefinic or acetylenic groups, which can also be directly silicon-bonded, especially the vinyl group.
- the other functional groups R 2 are bonded to the silicon atom via spacer groups, the spacer always being Si—C bonded.
- the spacer is a divalent hydrocarbon radical which comprises 1 to 30 carbon atoms and in which non-adjacent carbon atoms can be replaced by oxygen atoms and which may also contain other heteroatoms or heteroatom groups, although this is not preferred.
- the methacrylate group, the acrylate group and the epoxy group are preferably bonded via a spacer, the spacer being composed of a divalent hydrocarbon radical comprising 3 to 15 carbon atoms, in particular 3 to 8 carbon atoms, in particular 3 carbon atoms and optionally also at most one to 3 oxygen atoms, preferably at most 1 oxygen atom bonded to the silicon atom.
- the carboxyl group is preferably attached via a spacer of preferably 3 to 30 carbon atoms, in particular 3 to 20 carbon atoms, in particular 3 to 15 carbon atoms and optionally also at most one to 3 oxygen atoms, preferably at most 1 oxygen atom, in particular no oxygen atom, to the divalent hydrocarbon radical Bonded silicon atom.
- Hydrocarbon radicals R 2 containing heteroatoms are, for example, carboxylic acid radicals of the general formula (II) Y 1 - COOH (II), where Y 1 is preferably a divalent linear or branched hydrocarbon radical having up to 30 carbon atoms, where Y 1 can also contain olefinically unsaturated groups or heteroatoms and the atom bonded directly to the silicon by the radical Y 1 is a carbon.
- Y 1 is preferably a divalent linear or branched hydrocarbon radical having up to 30 carbon atoms, where Y 1 can also contain olefinically unsaturated groups or heteroatoms and the atom bonded directly to the silicon by the radical Y 1 is a carbon.
- the radical Y 2 is preferably hydrocarbon radicals and accordingly, independently of R 1 , preferably has the meaning of R 1 .
- Y 2 can also contain further heteroatoms and organic functions such as double bonds or oxygen atoms, although this is not preferred.
- the carboxylic acid ester radical R 2 can also be bonded in the opposite direction, ie it can be a radical of the form Y 1 -OC ( ⁇ O)Y 2 .
- organofunctional radicals R 2 are acryloxy or methacryloxy radicals of methacrylic acid esters or acrylic acid esters such as methyl acrylate, methyl methacrylate, ethyl acrylate, ethyl methacrylate, propyl acrylate, propyl methacrylate, n-butyl acrylate, n-butyl methacrylate, isobutyl acrylate, isobutyl methacrylate, t-butyl acrylate , t-butyl methacrylate, 2-ethylhexyl acrylate and norbornyl acrylate.
- methacrylic acid esters or acrylic acid esters such as methyl acrylate, methyl methacrylate, ethyl acrylate, ethyl methacrylate, propyl acrylate, propyl methacrylate, n-butyl acrylate, n-butyl methacrylate, isobutyl acryl
- Methyl acrylate, methyl methacrylate, n-butyl acrylate, iso-butyl acrylate, t-butyl acrylate, 2-ethylhexyl acrylate, and norbornyl acrylate are particularly preferred.
- a particularly preferred radical (XIII) is the vinyl radical, the propenyl radical and the butenyl radical, in particular the vinyl radical.
- the radical (XIII) can also denote a dienyl radical bonded via a spacer, such as the 1,3-butadienyl radical bonded via a spacer or the isoprenyl radical.
- organofunctional radicals R 2 are carboxylic acid-functional, vinyl-functional and epoxy-functional radicals and the hydrogen radical.
- the vinyl and hydrogen residue are particularly preferred organofunctional radicals R 2
- the silicone resins (i) carry different organofunctional groups.
- the selected organic groups do not react with one another under the conditions of regular storage, ie storage for 6 months at 23°C, 1013 mbar in airtight and moisture-tight sealed containers.
- combinations of vinyl groups and Si-H groups are possible, since these require significantly different conditions than those of regular storage for their reaction with one another, for example a catalyst and high temperature.
- a suitable choice of combinations of functional groups can easily be derived by the person skilled in the art from the published literature on the chemical reactivity of organofunctional groups.
- a particularly preferred combination of different organofunctional groups is that of hydridic hydrogen and olefinically unsaturated group, in the particularly preferred form of which the olefinically unsaturated group is directly silicon-bonded.
- the most preferred olefinically unsaturated group is the vinyl group.
- radicals R.sup.1 or R.sup.2 are present in a unit of the formula (Ic), these can independently represent different radicals within the specified group of possible radicals, the aforementioned conditions for the organofunctional groups having to be observed.
- R 17 has the meaning of R 1 or can be an -OH.
- Preferred hydrocarbon radicals R 1 are unsubstituted hydrocarbon radicals having 1 to 16 carbon atoms.
- Selected examples of hydrocarbon radicals R 1 radicals are alkyl radicals, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, iso -Pentyl, neopentyl, tert-pentyl, hexyl, such as n-hexyl, heptyl, such as n-heptyl, octyl, such as n-octyl, and iso-octyl, such as 2,2,4-trimethylpentyl, Nonyl radicals such as the n-nonyl radical, decyl radicals such as the n-decyl radical,
- the powdered fillers are preferably finely divided granules consisting of many small, solid particles such as grains or spheres.
- the average particle size of the pulverulent fillers is preferably 0.1 ⁇ m to 0.3 mm, particularly preferably 0.5 ⁇ m to 100 ⁇ m, in particular 2 ⁇ m to 20 ⁇ m.
- Examples of pulverulent fillers are non-reinforcing fillers, ie fillers with a BET surface area of up to 50 m 2 /g, such as quartz, diatomaceous earth, calcium silicate, zirconium silicate, zeolites, metal oxide powders such as aluminum, titanium, iron or zinc oxides or their mixed oxides, barium sulfate, calcium carbonate, gypsum, silicon nitride, silicon carbide, boron nitride, glass and plastic powder; reinforcing fillers, ie fillers with a BET surface area of at least 50 m 2 /g, such as pyrogenic silica, precipitated silica, carbon black, such as furnace and acetylene black and silicon-aluminum mixed oxides with a large BET surface area.
- non-reinforcing fillers ie fillers with a BET surface area of up to 50 m 2 /g, such as quartz, diatomaceous earth, calcium
- the fillers mentioned can be rendered hydrophobic, for example by treatment with organosilanes or siloxanes or by etherification of hydroxyl groups to form alkoxy groups.
- One type of powdered filler can be used, or a mixture of at least two powdered fillers can be used.
- the powdered filler can also be a pigment, such as earth pigments, eg chalk, ochre, umber, green earth, mineral pigments such as titanium dioxide, chrome yellow, red lead, zinc yellow, zinc green, cadmium red, cobalt blue, organic pigments such as sepia, Kassel brown, indigo, azo -pigments, anthraquinoids-, Indigoid, dioxazine, quinacridone, phthalocyanine, isoindolinone and alkali blue pigments, with many of the inorganic pigments also functioning as fillers and vice versa.
- earth pigments eg chalk, ochre, umber, green earth
- mineral pigments such as titanium dioxide, chrome yellow, red lead, zinc yellow, zinc green, cadmium red, cobalt blue
- organic pigments such as sepia, Kassel brown, indigo, azo -pigments, anthraquinoids-, Indigoid, dioxazine,
- the fibrous fillers preferably consist of particles in which the average length to diameter ratio is preferably at least 5:1, particularly preferably at least 8:1, particularly at least 12:1 and preferably at most 10,000:1, particularly preferably at most 1000:1 .
- fibrous fillers are natural fibres, such as plant fibres, e.g. cotton, bamboo, nettle, hemp or linen fibres, animal fibres, e.g. wool, alpaca, camel hair, cashmere, silk or mohair fibers and mineral fibres, e.g. asbestos, erionite, attapulgite, sepiolite and wollastonite.
- plant fibres e.g. cotton, bamboo, nettle, hemp or linen fibres
- animal fibres e.g. wool, alpaca, camel hair, cashmere, silk or mohair fibers
- mineral fibres e.g. asbestos, erionite, attapulgite, sepiolite and wollastonite.
- fibrous fillers are chemical fibers such as fibers made from natural polymers, e.g. fibers made from regenerated cellulose such as viscose, modal, e.g. fibers made from cellulose esters such as acetate and triacetate, e.g. modified protein fibers such as protein fibers from regenerated natural protein of vegetable or animal origin soybean protein fiber and casein fibers such as polylactide, alginate and chitin; fibers of synthetic polymers such as polyester, polyamide, polyimide, polyamideimide, aramid, polyacrylic, PTFE, polyethylene, polypropylene, melamine and polystyrene; Fibers made from inorganic substances such as ceramic, glass, quartz, carbon, metal fibers.
- natural polymers e.g. fibers made from regenerated cellulose such as viscose
- modal e.g. fibers made from cellulose esters such as acetate and triacetate
- modified protein fibers such as protein fibers from re
- the silicone resin composition (S) may contain hydrosilylation catalyst. Everyone can do this known catalysts are used, which catalyze the hydrosilylation reactions taking place during the crosslinking of addition-crosslinking silicone compositions.
- the hydrosilylation catalyst which is preferably selected from metals and their compounds such as platinum, rhodium, palladium, ruthenium and iridium, preferably platinum. Platinum and platinum compounds are preferably used. Those platinum compounds which are soluble in polyorganosiloxanes are particularly preferred.
- Soluble platinum compounds which can be used are, for example, the platinum-olefin complexes of the formulas (PtCl 2 ⁇ olefin) 2 and H(PtCl 3 ⁇ olefin), preference being given to alkenes having 2 to 8 carbon atoms, such as ethylene, propylene, isomers of butene and octene , Or cycloalkenes having 5 to 7 carbon atoms, such as cyclopentene, cyclohexene and cyclo-heptene, are used.
- Platinum-cyclopropane complex of the formula (PtCl 2 C 3 H 6 ) 2 , the reaction products of hexachloroplatinic acid with alcohols, ethers and aldehydes or mixtures thereof, or the reaction product of hexachloroplatinic acid with methylvinylcyclotetrasiloxane in the presence of Sodium bicarbonate in ethanolic solution.
- Complexes of platinum with vinylsiloxanes, such as sym-divinyltetramethyldisiloxane are particularly preferred.
- the hydrosilylation catalyst can be used in any form, for example also in the form of microcapsules containing hydrosilylation catalyst, or polyorganosiloxane particles.
- the content of hydrosilylation catalysts is preferably chosen so that the silicone resin composition (S) has a Pt content from 0.1-200 ppm by weight, preferably from 0.5-40 ppm by weight.
- the silicone resin composition (S) may contain peroxide as a crosslinking agent.
- peroxide examples are dibenzoyl peroxide, bis(2,4-dichlorobenzoyl) peroxide, dicumyl peroxide and 2,5-bis(tert-butylperoxy)-2,5-dimethylhexane and mixtures thereof, where bis(2,4-dichlorobenzoyl) -peroxide and 2,5-bis(tert-butylperoxy)-2,5-dimethylhexane are preferred.
- the peroxide content is preferably chosen such that the silicone resin composition (S) has a peroxide content of 0.1 to 5% by weight, preferably 0.5-2% by weight.
- the silicone resin composition can be cured purely via a hydrosilylation catalyst, peroxide, or with a combination of hydrosilylation catalyst and peroxide.
- a combination of hydrosilylation catalyst and peroxide is precured with hydrosilylation catalyst at a lower temperature, for example 100°C to 150°C, and postcured with epoxy at a higher temperature, for example 160°C to 210°C, or only at a single temperature of, for example 150°C to 200°C cured without pre-curing.
- the silicone resin composition (S) can contain other components, such as plasticizers, adhesion promoters, soluble dyes, inorganic and organic pigments, fluorescent dyes, solvents as already mentioned above, fungicides, fragrances, dispersing agents, rheological additives, corrosion inhibitors, oxidation inhibitors, light stabilizers, heat stabilizers, flame retardants making means, means of influencing the electrical properties and means of improving thermal conductivity.
- plasticizers such as plasticizers, adhesion promoters, soluble dyes, inorganic and organic pigments, fluorescent dyes, solvents as already mentioned above, fungicides, fragrances, dispersing agents, rheological additives, corrosion inhibitors, oxidation inhibitors, light stabilizers, heat stabilizers, flame retardants making means, means of influencing the electrical properties and means of improving thermal conductivity.
- solvents that can be used are ethers, especially aliphatic ethers such as dimethyl ether, diethyl ether, methyl t-butyl ether, diisopropyl ether, dioxane or tetrahydrofuran, esters, especially aliphatic esters such as ethyl acetate or butyl acetate, ketones, especially aliphatic ketones such as acetone or methyl ethyl ketone, sterically hindered alcohols, in particular aliphatic alcohols such as i-propanol, t-butanol, amides such as DMF, aromatic hydrocarbons such as toluene or xylene, aliphatic hydrocarbons such as pentane, cyclopentane, hexane, cyclohexane, heptane, chlorinated hydrocarbons such as methylene chloride or chloroform.
- ethers especially aliphatic ether
- Solvents or solvent mixtures with a boiling point or boiling range of up to 120° C. at 0.1 MPa are preferred.
- the solvents are preferably aromatic or aliphatic hydrocarbons.
- the silicone resins (i) in the silicone resin composition (S) are crosslinked by hydrosilylation catalysts or by peroxides and, depending on the selection of the organofunctional groups present, can also take place by further reactions such as condensation reactions or polymerization reactions.
- the silicone resin composition (S) is particularly suitable for the production of hard, solid products, such as molded articles, for example electronic components and casting molds, flat structures, such as coatings, fillers for filling cavities, or the like.
- the molecular compositions are determined by means of nuclear magnetic resonance spectroscopy (for terminology, see ASTM E 386: High-resolution nuclear magnetic resonance spectroscopy (NMR): terms and symbols), the 1 H nucleus being measured.
- the viscosities are determined on an MCR302 rheometer from Anton Paar, Ostfildern, Germany, in accordance with DIN EN ISO 3219 in rotation with a cone-plate measuring system. The measurements are made in the Newtonian range of the samples. In the case of non-Newtonian behavior of the sample, the shear rate is also given. Unless otherwise stated, all viscosity data apply at 25°C and normal pressure of 1013 mbar.
- the flexural strength is determined in accordance with ISO 178 using a Texture Analyzer TA.HD.Plus from Stable Micro Systems. Test bars with the dimensions (80 ⁇ 10 ⁇ 4) mm 3 are placed on two supports and loaded with a moving stamp. To produce the test bars, the silicone resin composite is pressed for 10 minutes at 165° C. and the test bars produced in this way are then tempered at 200° C. for 24 hours after demoulding.
- the tensile strength is determined in accordance with ISO 527-2 using a Texture Analyzer TA.HD.Plus from Stable Micro Systems on test bars of type 1B. To produce the test bars, plates with a thickness of (4 ⁇ 0.2) mm are made of silicone resin composite pressed for 10 minutes at 165°C and tempered for 24 hours at 200°C after demoulding. The test rods are milled out of these plates.
- TPh (C 6 H 5 )SiO 3/2 )
- MH H(CH 3 ) 2 SiO 1/2
- VM (C 2 H 3 ) (CH 3 ) 2 SiO 1/2 )
- the fillers are mixed in homogeneously.
- 1 part by weight of 2,5-(tert-butylperoxy)-2,5-dimethylhexane is mixed in with this and pressed at 165°C. After another 24 hours of storage at 200 °C, the material is fully cured.
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- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Claims (9)
- Composition de résine de silicone (S),
qui contient une résine de silicone (i) constituée de motifs de formules générales (Ia), (Ib), (Ic) et (Id)dans lesquellesR1 représente des radicaux hydrocarbonés monovalents identiques ou différents les uns des autres ou -OH,R2 représente des radicaux hydrocarbonés organofonctionnels monovalents identiques ou différents les uns des autres, des radicaux hydrocarbonés à insaturation oléfinique ou un radical hydrogène, le radical R2 étant lié à l'atome de silicium par l'intermédiaire d'un atome de carbone et, lorsque R2 représente un radical hydrogène, ce dernier étant directement lié à l'atome de silicium,c représente les valeurs 0 ou 1,à la condition que- au moins 5 % en moles des motifs (Ic) soient présents,- au moins 20 % en moles des motifs (Ia) soient présents,- au plus 20 % en moles des motifs (Ib) soient présents,- au plus 20 % en moles des motifs (Id) soient présents,- au moins 1 % en moles des motifs (Ic) comprennent un radical R2 représentant l'atome d'hydrogène,- et au moins 1 % en moles des motifs (Ic) comprennent un radical R2 , qui représente un radical hydrocarboné à insaturation oléfinique,et contient des charges, tant pulvérulentes que fibreuses. - Composition de résine de silicone (S) selon la revendication 1, dans laquelle, dans la résine de silicone (i), dans les motifs de Formule générale (Ic), le rapport entre le radical R2 qui représente un radical hydrocarboné à insaturation oléfinique et le radical R2 qui représente un radical hydrogène, est de 3:1 à 1:2.
- Composition de silicone (S) selon l'une ou plusieurs des revendications précédentes, dans laquelle les charges pulvérulentes présentent une granulométrie moyenne de 0,1 µm à 0,3 mm.
- Composition de silicone (S) selon l'une ou plusieurs des revendications précédentes, dans laquelle les charges pulvérulentes sont choisies parmi les charges ayant une aire BET allant jusqu'à 50 m2/g et les charges ayant une aire BET d'au moins 50 m2/g.
- Composition de silicone (S) selon l'une ou plusieurs des revendications précédentes, dans laquelle les charges fibreuses sont constituées de particules dans lesquelles le rapport moyen de la longueur au diamètre est d'au moins 5:1.
- Composition de silicone (S) selon l'une ou plusieurs des revendications précédentes, dans laquelle les charges fibreuses sont choisies parmi les fibres naturelles, les fibres chimiques et les fibres de matières inorganiques.
- Composition de silicone (S) selon l'une ou plusieurs des revendications précédentes, qui contient un catalyseur d'hydrosilylation, qui est choisi parmi les métaux et leurs composés du platine, du rhodium, du palladium, du ruthénium et de l'iridium.
- Composition de silicone (S) selon l'une ou plusieurs des revendications précédentes, qui contient un peroxyde en tant qu'agent de réticulation.
- Produits solides fabriqués à partir de compositions de silicone (S) selon l'une ou plusieurs des revendications précédentes.
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EP (1) | EP3969516B1 (fr) |
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JP2014065900A (ja) * | 2012-09-07 | 2014-04-17 | Dow Corning Toray Co Ltd | 硬化性シリコーン組成物およびその硬化物 |
DE102013217220A1 (de) * | 2013-08-28 | 2015-03-05 | Wacker Chemie Ag | Härtbare Organopolysiloxanzusammensetzungen |
CN104327507A (zh) * | 2014-09-15 | 2015-02-04 | 杭州师范大学 | 一种有机硅树脂模塑料及其制备方法 |
DE102014218918A1 (de) * | 2014-09-19 | 2016-03-24 | Wacker Chemie Ag | Verfahren zur Herstellung von organofunktionellen Siliconharzen |
DE102015200704A1 (de) * | 2015-01-19 | 2016-07-21 | Wacker Chemie Ag | Verfahren zur Herstellung von Siliconharzen |
WO2016136243A1 (fr) * | 2015-02-25 | 2016-09-01 | 東レ・ダウコーニング株式会社 | Composition de silicone granulaire durcissable et son procédé de préparation |
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